N,N,N',N'-Tetramethylethylenediamine → 1-[2,5-Dimethoxy-3,6-bis(methoxymethoxy)phenyl]-5-[2,5-dimethoxy-3,6-bis(methoxymethoxy)-4-iodophenyl]pentane

温度

-78 °C

1.53 Grams of 2,2'-pentamethylenebis[1,4-dimethoxy-3,6-bis(methoxymethoxy)benzene] was dissolved in a mixed solvent of 40 ml of tetrahydrofuran with 4 ml of hexamethylphosphoric triamide, to this solution was added 0.79 ml of N,N,N',N'-tetramethylethylenediamine, then this mixture was cooled to -78° C. on a dry ice-acetone mixture bath. 3.49 Milliliters of n-butyllithium (1.6 M, n-hexane solution) was added dropwise to the reaction mixture and stirred for 30 minutes. Next, 15 ml of tetrahydrofuran solution containing 1.18 g of N-iodosuccinimide was added dropwise and the reaction mixture was stirred overnight. The solvent was removed under reduced pressure, and the residue obtained was extracted twice with 100 ml of diethyl ether, and the diethyl ether layer was washed twice with 100 ml of water, and washed twice with 100 ml of a saturated sodium chloride aqueous solution, then dried over anhydrous magnesium sulfate. The dried diethyl ether extract was concentrated under reduced pressure, the residue obtained was purified by means of a separative thin layer chromatography (thickness: 2 mm, adsorbent: Merk 5717 silica gel, developing solvent: ethyl acetate-dichloromethane (1:9). There were obtained 685 mg of 1-[2,5-dimethoxy-3,6-bis(methoxymethoxy)phenyl]-5-[2,5-dimethoxy-3,6-bis(methoxymethoxy)-4-iodophenyl]pentane, as well as 575 mg of 2,2'-pentamethylenebis[1,4-dimethoxy-3,6-bis(methoxymethoxy)-5-iodobenzene].

1. additionwas added dropwise
2. stirringthe reaction mixture was stirred overnight
3. customThe solvent was removed under reduced pressure
4. customthe residue obtained
5. extractionwas extracted twice with 100 ml of diethyl ether
6. washthe diethyl ether layer was washed twice with 100 ml of water
7. washwashed twice with 100 ml of a saturated sodium chloride aqueous solution
8. dry with materialdried over anhydrous magnesium sulfate
9. extractionThe dried diethyl ether extract
10. concentrationwas concentrated under reduced pressure
11. customthe residue obtained
12. customwas purified by means of a separative thin layer chromatography (thickness

ORDレコード

ord-9a48f1bc0465496ab9b80a232d11e620

出典データセット

uspto-grants-1993_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05220042